Sr. Manager, Enterprise Program Management

Five Below•Philadelphia, PA

About The Position

At Five Below, our growth is fueled by our purpose: 'We know life is way better when you are free to Let Go & Have Fun in an amazing experience, filled with unlimited possibilities, priced so low, you can always say yes to the newest, coolest stuff!' This role is crucial in translating our enterprise strategy into actionable plans and ensuring successful execution of high-priority, enterprise-wide initiatives. You will lead end-to-end program management, coordinate diverse functional workstreams, and drive timely completion of commitments while maintaining rigor around scope, schedule, budget, risk, quality, and benefits. This position also involves supporting the PMO's operations, ensuring effective executive governance and communication, managing risks and dependencies, facilitating business transformation and operationalization, and developing PMO standards and capabilities. Success in this role means providing senior leadership with accurate, decision-ready information, fostering alignment and transparency across cross-functional teams, and ensuring major initiatives are successfully operationalized and reviewed post-implementation. The ideal candidate will be a strategic thinker with strong program management fundamentals and the ability to influence senior stakeholders.

Requirements

Bachelor’s degree in business, operations, finance, technology, project management, or a related field.
7+ years of experience in enterprise program management, PMO leadership, business transformation, management consulting, strategic planning, or a related discipline.
Demonstrated experience leading complex, cross-functional programs with significant business impact and senior-leader visibility.
Experience supporting PMO operating models, governance cadences, program standards, reporting routines, or execution frameworks.
Strong command of program-management fundamentals, including integrated planning, critical-path management, RAID, dependency management, change control, resource planning, and benefits realization.
Proven ability to influence and align senior stakeholders and functional leaders without direct authority.
Experience translating strategy into practical execution plans, operating models, adoption plans, and measurable outcomes.
Excellent executive communication, facilitation, written communication, analytical, and organizational skills.
Strong business judgment and comfort making recommendations in ambiguous, fast-moving environments.
Ability to manage multiple priorities while maintaining attention to detail and a clear focus on enterprise outcomes.
Experience working across business and technology teams is preferred.

Nice To Haves

Advanced degree is a plus.
PMP or comparable certification is preferred but not required.

Responsibilities

Lead end-to-end program management for high-priority, enterprise-wide initiatives from definition and planning through implementation, adoption, and sustained value realization.
Translate enterprise strategy into integrated roadmaps, milestones, workplans, decision points, resource requirements, and measurable outcomes.
Coordinate business, technology, finance, people, operations, and other functional workstreams to maintain alignment and execution momentum.
Establish clear scope, objectives, roles, decision rights, success measures, and escalation paths for each program.
Manage interdependencies across workstreams, functions, vendors, systems, and organizational changes.
Drive timely completion of commitments while maintaining appropriate rigor around scope, schedule, budget, risk, quality, and benefits.
Support the Senior Director in operating the PMO and preparing the information, analysis, and recommendations needed for effective enterprise decision-making.
Maintain an integrated view of active programs that clearly communicates initiative health, milestones, dependencies, risks, decisions, resource needs, and expected outcomes.
Coordinate information across program teams so leadership has a consistent, accurate understanding of progress and emerging concerns.
Ensure decisions are documented, communicated, assigned to accountable owners, and followed through to closure.
Continuously improve PMO standards, operating cadences, and reporting practices so they enable speed, transparency, and execution without creating unnecessary bureaucracy.
Design and manage operating cadences for steering committees, executive reviews, core teams, workstream meetings, and other governance forums.
Develop concise, decision-oriented executive materials, including status updates, pre-reads, portfolio views, risk summaries, milestone reviews, and recommendation papers.
Facilitate meetings that drive decisions, resolve issues, clarify ownership, and maintain alignment across a complex stakeholder group.
Serve as an objective integrator: bring forward clean recommendations and escalations while ensuring the appropriate business leader remains the decision-maker.
Tailor communication for different audiences, from executive leadership to functional owners and extended project teams.
Establish and maintain disciplined RAID management across enterprise programs and portfolios.
Identify emerging risks, cross-functional dependencies, decision gaps, and delivery constraints before they affect critical milestones.
Partner with workstream and functional leaders to develop mitigation plans, resolve issues, and escalate items at the right altitude.
Monitor changes in scope, sequencing, assumptions, resources, and business context; assess impact and recommend adjustments.
Create transparency around tradeoffs and ensure that risks and decisions are connected to the enterprise outcomes they may affect.
Help teams move initiatives beyond launch by planning for adoption, process ownership, capability building, communications, training, and ongoing performance management.
Partner with initiative sponsors and functional owners to define future-state processes, operating models, handoffs, and governance.
Ensure transformation programs are practical, scalable, and sustainable within the operating environment.
Establish and lead a disciplined post-implementation hindsighting process that compares intended outcomes with actual results, including adoption, business performance, operational impact, timing, cost, and stakeholder experience.
Facilitate structured post-implementation reviews with sponsors, workstream leaders, and delivery partners to identify root causes, lessons learned, repeatable practices, and improvement opportunities.
Translate hindsight findings into clear recommendations, action owners, and follow-up commitments; track those actions through closure and feed the learning into future program planning and PMO standards.
Use data and stakeholder insight to identify opportunities to simplify work, reduce friction, and strengthen the organization’s ability to deliver change.
Develop and maintain practical PMO standards, templates, playbooks, dashboards, and tools for planning, reporting, governance, and execution.
Coach project leaders on integrated planning, milestone management, risk and dependency management, stakeholder engagement, change control, and executive communication.
Help build a consistent, service-oriented PMO experience across functions while adapting the level of process to the size, complexity, and risk of each initiative.
Contribute to PMO capability assessments, operating-model design, resource planning, and continuous improvement.